Good suggestion by @Drew Sygit to consider section 8 tenants for possible cashflow and lower vacancy. 

With now being a weekend, and going on Christmas week, what would you suggest i do?

If you have lived in it for 2 yrs I would suggest renting it for 2 - 3 years and then selling it to avoid capital gains taxes. 

What markets would you suggest looking at?

I would suggest Indy.

The insurance is for a rental condo property located in Madison, Wisconsin I’m wondering if anyone knows of any other insurance company.

Thoughts and suggestions or too complex and take the hit on capital gains tax as I sell my rentals?

I highly suggest you use our marketplaces to find trusted, investor-friendly team members: Tax Pro finder: https://www.biggerpockets.com/business/finder/tax-and-financ...Lender finder: https://www.biggerpockets.com/business/finder/lendersProperty manager finder (if you go that route and don't self manage): https://www.biggerpockets.com/business/finder/property-manag...

I suggest contacting an RE attorney who can assess your options.

Section A, you’ll see that owner-occupancy is required for the JADU.I wonder what happens if you’re house-hacking when you build the JADU.